Not only did she lose to Paul to add salt to the wound he calls her the weakest gym leader he ever fought even refering to badge as a lightweight badge. - egnomac

6Max gets upset after Ash beats Norman

Max loves and respects his dad Norman and gets really upset after he loses to Ash that he takes the badge and locks himself behind a door until Norman tells him that losing is a very important part of bieng a gym leader and all battles in general. - egnomac

7Misty's decision to stay with Rudy or stay with Ash

Rudy clearly loves Misty at first she enjoys all the affection she gets from him but when he asks her to stay with him her mood completly changes she becomes very worried over the tough descion to stay with Rudy or continue traveling with Ash eventually she makes her choice pretty clear when she cheers for Ash - egnomac

8Haunter gets Sabrina to laugh

9Ash loses the Ritchie after Charizard refuses to battle

10May loses to Drew in her contest debut

The Contenders

11Bye Bye Butterfree

How is this an emotional moment? I felt nothing for Butterfree leaving because it was such a forgettable Pokémon with weak personality.

12The end of XYZ

The best season of the anime ends so emotionally, all of the characters go their own routes.